CN109438442B - Indole compound, and synthesis method and application thereof - Google Patents

Indole compound, and synthesis method and application thereof Download PDF

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CN109438442B
CN109438442B CN201811465069.6A CN201811465069A CN109438442B CN 109438442 B CN109438442 B CN 109438442B CN 201811465069 A CN201811465069 A CN 201811465069A CN 109438442 B CN109438442 B CN 109438442B
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朱瑞
郑绍军
唐冰
蔡星伟
杨丹丹
刘苏苏
滕新洁
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Abstract

The invention relates to an indole compound, a synthesis method and application thereof. The general formula of the indole compound is

Description

Indole compound, and synthesis method and application thereof
Technical Field
The invention aims to provide an indole compound, a synthetic method thereof and application thereof in antifouling aspects such as ships, wharf equipment, marine drilling platform pillars and the like.
Background
Facilities below a water level line such as ships and docks are contacted with seawater for a long time and are attached by marine organisms, and the attachment and deposition of marine fouling organisms on underwater facilities can result in the increase of ship resistance, the acceleration of metal corrosion, the failure of instruments, the blockage of pipelines and the like, so that the performance and the service life of the underwater facilities are seriously influenced, and huge economic loss is caused. The marine biofouling problem is a difficult obstacle for mankind to conquer the sea because of the extreme vitality of marine life. The antifouling paint for ship hull is a paint material with special effect, and when it is painted onto ship hull, the ship hull can look beautiful, resist corrosion of sea and prevent collision and damage of sea life to ship hull. The antifouling paint is generally coated on the antirust paint of marine underwater facilities and ship bottoms and is positioned on the outermost layer. The main function of the paint is to gradually release poison in the modes of hydrolysis, diffusion or seepage of the poison in the paint film, and the like, thereby achieving the purpose of preventing marine organisms from attaching to marine underwater facilities or ship bottoms. The antifouling paint containing toxic antifouling agents such as organic tin and the like can effectively prevent marine organisms from attaching, but the antifouling paint has high efficiency in antifouling and seriously harms the marine ecological environment. The International Maritime Organization (IMO) has clearly regulated that the use of organotin-containing antifouling paints has been prohibited globally since 1 month and 1 day of 2008. Copper-containing self-polishing antifouling paints are currently the best replacement for organotin paints, but studies have found that copper ions also accumulate in large quantities in the ocean, particularly in harbors, disrupting ecological balance. Therefore, copper-containing antifouling paints will eventually be banned as well.
In order to reduce the pollution damage, the research on the environment-friendly ship antifouling technology is carried out in many countries, and certain results are obtained. The antifouling paint for painting is the most widely applied method due to the outstanding advantages of good antifouling effect, strong feasibility, low one-time investment, no need of management and the like, and the antifouling paint is almost adopted for ship antifouling at present. The antifouling paint is mainly composed of five major parts of resin, antifouling agent, filler, solvent and auxiliary material, and is coated on the surface of a ship and the like to form an antifouling layer after being fully mixed. Of these, the antifouling agent is the most predominant, most effective component, being the core of the antifouling paint. The antifouling paint plays a role in preventing marine organisms from attaching to the surface of an object through the controllable release of the antifouling agent and the action of the antifouling paint and the marine fouling organisms.
Among the environmental antifouling agents, the research on bioactive natural products as antifouling agents is receiving more and more attention. The natural product antifouling agent is a natural substance extracted from various land plants and marine animals and plants, can be degraded quickly, does not harm the life of organisms, and is favorable for keeping ecological balance11. The effective components of the natural product antifouling agent can be slowly and uniformly released through the control of a slow release technology, so that the aims of long-acting pollution-free antifouling are fulfilled.
The research on natural antifouling agents began in the 60's of the 20 th century, but the yield of the natural antifouling agents was far from the development of the human society because of the limitations of various factors such as biomass, extraction cost and separation technology, and therefore, artificial synthetic antifouling agents have come into play. The artificial anti-fouling agent is an anti-fouling agent which is artificially synthesized by chemical means and contains a natural product structure or an analogue structure thereof. Through the diligent efforts of scientists, the research and development of the artificially synthesized anti-fouling agent have achieved fruitful results.
Indole antifouling agents are the most promising antifouling agents so far, and research on indole compounds as antifouling agents has been greatly advanced, however, research on indole antifouling agents is mainly focused on indole-3-formaldehydes with substituents at the 3-position and arundoin compounds at present, and research on the antifouling activity of indole compounds with other structures is not reported in detail, so that development of an economic and efficient method for synthesizing indole compounds brings great economic and social benefits to development in the field.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide an indole compound, a synthesis method and application thereof, the synthesis process is simple, the product purity is high, and the indole compound has good antifouling activity on various bacteria.
In order to achieve the purpose of the invention, the invention adopts the following technical scheme:
indoles having the general formula (I):
Figure GDA0003208120570000031
the synthetic route for indoles having formula (I) is as follows:
Figure GDA0003208120570000032
r1 is any one of the following groups:
Figure GDA0003208120570000041
specifically, the synthesis process of the indole compound with the formula (I) comprises the following steps:
adding anhydrous pyridine into a substrate 9-methyl-1, 2,3,4,9,9 a-6H-4 aH-pyrido [2,3-b ] indol-4 a-ol to dissolve, slowly dropwise adding a reaction reagent acetic anhydride into the mixture, tracking and detecting by TLC (thin layer chromatography), dropwise adding a proper amount of methanol into a reaction solution until the reaction is completed, quenching the reaction, concentrating under reduced pressure to remove the methanol and the pyridine, combining organic phases, concentrating under reduced pressure, and separating a crude product by column chromatography to obtain the N-position acetylated derivative 1(R1 ═ the product of the group 1).
(R1 ═ products of groups 1-8) are chimonanthus nitens analogs, the synthesis method is the same as the above method, the difference is that different acids or acid anhydrides are added, and the reaction conditions and properties are shown in Table 1:
TABLE 1
Figure GDA0003208120570000042
The indole compound with the general formula (I) has good bactericidal activity, and the fungi are staphylococcus aureus, ralstonia solanacearum and bacillus cereus.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the indole compound provided by the invention has the advantages of simple structure, easily obtained raw materials, mild reaction conditions and simple process, and is suitable for antifouling application.
(2) The hexahydropyrroloindole compound provided by the invention has higher antifouling activity than TBTO.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1
Figure GDA0003208120570000051
Synthesis of (2)
Compound 1. weighing 200mg of substrate 9-methyl-1, 2,3,4,9,9 a-6H-4 aH-pyrido [2,3-b ]]Placing indole-4 a-alcohol in a 50mL dry round-bottom flask, adding 5mL anhydrous pyridine, stirring for dissolving, placing the system in an ice water bath at 0 ℃, slowly dropwise adding 0.07mL (0.72mmol) of acetic anhydride as a reaction reagent, moving to room temperature after complete dropwise addition, performing TLC tracking detection, adding a proper amount of methanol into the reaction solution after complete reaction, quenching the reaction, concentrating under reduced pressure to remove methanol and a small amount of pyridine, extracting with ethyl acetate for 3 times, combining organic phases, and sequentially using saturated CuSO to dissolve the organic phases4Washing with 3 times of solution, 3 times of saturated NaCl solution, anhydrous NaSO4And (5) drying. Concentrated under reduced pressure and the crude product isolated by column chromatography (PE: EA ═ 6:1) to yield 216mg of N-acetylated derivative 1 (96%).
And (3) character identification: the mixture is colorless and oily,1H-NMR(400MHz,CDCl3),δ7.34–7.14(m,2H),6.90–6.47(m,2H),5.24(s,1H),4.45–3.57(m,1H),3.31–3.22(m,1H),2.81(ddd,J＝13.2,8.5,4.8Hz,1H),2.64(d,J＝27.4Hz,3H),2.19(d,J＝11.1Hz,3H),2.02–1.71(m,2H),1.70–1.22(m,2H).13C NMR(100MHz,CDCl3)δ172.30(C),149.52(C),133.33(C),129.52(CH),129.36(CH),122.05(CH),119.11(CH),108.34(CH),86.45(C),41.96(CH2),37.14(CH3),33.31(CH2),22.14(CH3),19.02(CH2).MS(ESI(+))calcd for C14H18N2O2[M+H]+:246.3；found:247.0。
example 2
Figure GDA0003208120570000061
Synthesis of (2)
The compound 2 was a colorless oil,1H-NMR(400MHz,CDCl3),δ7.34–7.04(m,2H),6.86–6.46(m,2H),5.30(s,1H),4.45–3.63(m,1H),3.29–3.17(m,1H),2.81(ddd,J＝13.1,8.3,4.8Hz,1H),2.64(d,J＝25.6Hz,3H),2.58–2.34(m,2H),1.96–1.72(m,2H),1.67–1.24(m,2H),1.17(dt,J＝10.0,7.4Hz,3H).13C NMR(100MHz,CDCl3)δ175.45(C),149.54(C),133.41(C),129.52(CH),129.33(CH),122.04(CH),119.06(CH),108.34(CH),85.36(C),40.95(CH2),37.20(CH3),33.29(CH2),27.06(CH2),19.06,9.60(CH3).MS(ESI(+))calcd for C15H20N2O2[M+H]+:260.3；found:261.0。
example 3
Figure GDA0003208120570000062
Synthesis of (2)
The compound 3 was a pale yellow oil,1H-NMR(400MHz,CDCl3),δ7.26(s,2H),6.84–6.45(m,2H),5.30(s,1H),4.44–3.62(m,1H),3.22(ddt,J＝13.2,9.2,4.2Hz,1H),3.01(s,1H),2.80(ddd,J＝13.1,8.3,4.8Hz,1H),2.63(d,J＝32.5Hz,3H),2.55–2.23(m,2H),1.96–1.74(m,2H),1.73–1.35(m,3H),0.96(dt,J＝10.8,7.4Hz,3H).13C NMR(100MHz,CDCl3)δ174.68(C),149.54(C),133.48(C),129.27(CH×2),122.03(CH),119.02(CH),108.30(CH),85.35(C),41.10(CH2),37.11(CH3),35.31(CH2),32.91(CH2),19.40(CH2),18.54(CH2),13.96.(CH3).MS(ESI(+))calcd for C16H22N2O2[M+H]+:274.4；found:275.1。
example 4
Figure GDA0003208120570000071
Synthesis of (2)
Compound 4, a colorless oil,1H-NMR(400MHz,CDCl3),δ7.72–7.12(m,2H),6.83–6.50(m,2H),5.35(s,1H),4.44–3.71(m,1H),3.30–3.16(m,1H),2.92(dp,J＝9.8,6.7Hz,1H),2.79(ddd,J＝13.2,8.4,4.8Hz,1H),2.63(d,J＝26.5Hz,3H),1.98–1.83(m,1H),1.82–1.61(m,2H),1.55–1.37(m,1H),1.22–1.14(m,6H).13C NMR(100MHz,CDCl3)δ178.69(C),149.55(C),133.44(C),129.59(CH),129.32(CH),122.00(CH),119.02(CH),108.31(CH),84.92(C),40.74(CH2),37.14(CH3),33.60(CH2),31.07(CH),19.78(CH3×2),18.52(CH2).MS(ESI(+))calcd for C16H22N2O2[M+H]+:274.4；found:275.0。
example 5
Figure GDA0003208120570000081
Synthesis of (2)
Compound 5, a colorless oil,1H-NMR(400MHz,CDCl3),δ7.82–6.92(m,2H),6.88–6.44(m,2H),5.31(s,1H),4.49–3.61(m,2H),3.01(ddd,J＝13.1,8.8,5.5Hz,1H),2.63(d,J＝30.5Hz,3H),2.56–2.26(m,3H),1.95–1.72(m,2H),1.70–1.55(m,3H),1.41–1.33(m,2H),0.92(dt,J＝13.4,7.3Hz,3H).13C NMR(100MHz,CDCl3)δ175.01(C),149.52(C),133.47(C),129.49(CH),129.27(CH),122.05(CH),119.06(CH),108.32(CH),85.37(C),41.16(CH2),37.16(CH3),33.68(CH2),31.96(CH2),27.29(CH2),22.46(CH2),19.11(CH2),13.92(CH3).MS(ESI(+))calcd for C17H24N2O2[M+H]+:288.4；found:289.1。
example 6
Figure GDA0003208120570000082
Synthesis of (2)
Compound 6, a white solid,1H-NMR(400MHz,CDCl3),δ7.76–7.07(m,2H),6.86–6.46(m,2H),5.30(s,1H),4.44–4.05(m,1H),3.76–3.18(m,1H),3.00(s,1H),2.80(ddd,J＝13.1,8.3,4.8Hz,1H),2.63(d,J＝30.1Hz,3H),2.54–2.21(m,2H),1.96–1.72(m,2H),1.71–1.59(m,3H),1.36–1.29(m,4H),0.92–0.87(m,3H).13C NMR(100MHz,CDCl3)δ174.93(C),149.53(C),133.46(C),129.51(CH),129.28(CH),122.04(CH),119.04(CH),108.31(CH),85.37(C),41.13(CH2),37.13(CH3),33.96(CH2),33.06(CH2),31.75(CH2),25.11(CH2),22.49(CH2),19.11(CH2),14.01(CH3).MS(ESI(+))calcd for C18H26N2O2[M+H]+:302.4；found:303.1。
example 7
Figure GDA0003208120570000091
Synthesis of (2)
Compound 7, a light yellow oil,1H-NMR(400MHz,CDCl3),δ7.71–7.13(m,2H),6.84–6.43(m,2H),5.31(s,1H),4.43–4.03(m,1H),3.68(dt,J＝11.8,4.4Hz,1H),3.02(dddd,J＝13.2,8.7,4.5Hz,1H),2.64(d,J＝27.7Hz,3H),2.57–2.24(m,3H),1.96–1.71(m,2H),1.63(tdd,J＝14.8,11.4,7.3Hz,3H),1.32–1.27(m,6H),0.90–0.86(m,3H).13C NMR(100MHz,CDCl3)δ178.66(C),175.14(C),149.52(C),133.40(CH),129.29(CH),122.06(CH),119.08(CH),108.13(CH),85.38(C),41.17(CH2),37.17(CH3),33.92(CH2),33.09(CH2),31.67(CH2),29.03(CH2),25.18(CH2),22.57(CH2),19.09(CH2),14.03(CH3).MS(ESI(+))calcd for C19H28N2O2[M+H]+:316.4；found:317.1。
example 8
Figure GDA0003208120570000101
Synthesis of (2)
The compound 8 was a pale yellow oil,1H-NMR(400MHz,CDCl3),δ7.72–7.13(m,2H),6.87–6.24(m,2H),5.32(s,1H),4.46–4.03(m,1H),3.68(dt,J＝12.3,4.6Hz,1H),3.02(ddd,J＝13.1,8.6,4.4Hz,1H),2.64(d,J＝26.8Hz,3H),2.56–2.25(m,3H),1.97–1.73(m,2H),1.72–1.57(m,3H),1.31–1.26(m,8H),0.88(t,J＝4.7Hz,3H).13C NMR(100MHz,CDCl3)δ178.69(C),175.12(C),149.53(C),133.38(CH),129.31(CH),122.06(CH),119.08(CH),108.33(CH),85.39(C),41.16(CH2),37.16(CH3),33.92(CH2),33.08(CH2),31.79(CH2),29.45(CH2),29.03(CH2),25.22(CH2),22.61(CH2),19.09(CH2),14.08(CH3).MS(ESI(+))calcd for C20H30N2O2[M+H]+:330.5；found:331.2.
example 9: measurement of fungicidal Activity of Compounds obtained in examples 1 to 9
Microdilution method: the compounds obtained in examples 1 to 9 were dissolved in DMSO having a concentration of 1% to prepare solutions having a concentration of 1mg/mL, and the solutions were diluted by 2-fold series of concentrations to obtain sample solutions having a series of concentrations of 250.00, 125.00, 62.50, 31.25, 15.63, 7.81, 3.91, 1.96, 0.98, and 0.59. mu.g/mL, respectively. Adding 100 μ L of liquid culture medium into each well of 96-well plate, adding 100 μ L of sample solution into each well of experimental group for two-fold dilution, and adding 100 μ L of sample solution with concentration of 1 × 106spores/mLAdding 100 mu L of the bacterial liquid into the control group, covering the 96 holes with the bacterial liquid, sealing the control group with a membrane, placing the control group in a constant temperature incubator, culturing the bacteria at 37 ℃ for 24 hours, culturing the plant pathogenic fungi and the human pathogenic fungi at 28 ℃ for 48-72 hours, taking out a 96-hole plate, and reading the Minimum Inhibitory Concentration (MIC) value. According to the judgment, the detection results of the indole-containing compound on the two bacteria are shown in Table 2.
TABLE 2 MIC of Compounds against gram-negative bacteria
Figure GDA0003208120570000111
The MICs of the compounds 5 and 7 on the Ralstonia solanacearum are found to be 62.50 mu g/mL and are equivalent to positive control gentamicin (62.50 mu g/mL) and better than positive control streptomycin (250.00 mu g/mL) through activity analysis; MICs of compounds 2,3, 8 for Ralstonia solanacearum of 31.25. mu.g/mL were superior to positive controls gentamicin (62.50. mu.g/mL) and streptomycin (250.00. mu.g/mL). Has better inhibitory activity. Compounds 7 and 8 have inhibitory effects on Staphylococcus aureus and Bacillus cereus.

Claims (3)

1. Synthetic routes to indoles having the general formula (I):
Figure 958965DEST_PATH_IMAGE002
a compound of the formula (I),
r1 is any one of the following groups:
Figure DEST_PATH_IMAGE004A
the method is characterized by comprising the following reaction formula:
Figure 938423DEST_PATH_IMAGE006
(a) formula (I)
Adding anhydrous pyridine into a substrate (a) to dissolve, slowly dropwise adding reaction reagent acid or anhydride into the substrate, tracking and detecting by TLC (thin layer chromatography), dropwise adding methanol into a reaction solution to quench the reaction when the reaction is complete, concentrating under reduced pressure to remove methanol and pyridine, combining organic phases, concentrating under reduced pressure, and separating a crude product by column chromatography to obtain the product; the acid is valeric acid, caproic acid, enanthic acid or caprylic acid; the acid anhydride is propionic anhydride, butyric anhydride or isobutyric anhydride.
2. Use of the indoles of formula (I) as obtained in claim 1 for marine antifouling.
3. The use according to claim 2, wherein the bacteria involved in marine antifouling activity are Staphylococcus aureus, Ralstonia solanacearum, and Bacillus cereus.
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